Embark on a bespoke journey through Tuscany and Umbria, where every moment is tailored for an unforgettable experience.
Begin in Florence or Rome, where a charming English-speaking chauffeur awaits to transport you in a sleek Mercedes to Siena. As you leave the city, the Tuscan countryside unfolds with rolling hills, vineyards, and quaint villages, setting a serene tone for your arrival in Siena.
Here, a private walking tour through the medieval streets introduces you to the city's rich history, including the iconic Piazza del Campo and the stunning Cathedral, guided by an expert who reveals the secrets of this UNESCO World Heritage Site.
The next day, journey to Assisi, the birthplace of Saint Francis. Explore the grand Basilica of Saint Francis, marvel at its frescoes, and visit the sacred Porziuncola chapel. In the rolling hills of Umbria, visit a traditional oil mill to learn about the production of exquisite extra virgin olive oil, followed by a guided tasting and a delightful lunch. Your day continues in Montefalco, where you'll tour a renowned winery, savoring the robust Sagrantino wines that embody the essence of Umbria.
Conclude your adventure with a full-day tour through Tuscany's Chianti region and medieval treasures. Discover San Gimignano’s tower-filled skyline and explore its rich art and history. Wander through the scenic Chianti villages, famed for their exceptional wines, and finish in Monteriggioni, a perfectly preserved medieval walled town. This journey combines luxury, history, and culinary delights, ensuring an enriching and memorable
escape.
AT A GLANCE:
- Day 1: Luxurious Tuscan Escape: A Personalized Journey from Florence or Rome to the Heart of Siena
- Day 2: Sacred and Savory: A Private Day Trip from Siena to Assisi and the Flavors of Umbria
- Day 3: Timeless Tuscany: A Day Tour from Siena to San Gimignano, Chianti, and Monteriggioni
YOUR CUSTOMIZABLE 3 DAYS ITINERARY:
This itinerary serves as an example to help you plan a customized vacation with the help of our travel designer
Day 1: Luxurious Tuscan Escape: A Personalized Journey from Florence or Rome to the Heart of Siena
Imagine stepping off your flight or departing your elegant hotel in the heart of Florence or Rome, where a charming, impeccably dressed driver greets you with a warm smile. Your personal chauffeur, fluent in English, is prepared to whisk you away in the luxurious comfort of a sleek Mercedes.
As soon as you settle into the plush leather seats, the stress of travel begins to dissipate. Your driver, a consummate professional, knows the scenic routes and hidden gems, ensuring your journey to Siena is more than just a transfer—it's a memorable experience.
As you glide smoothly out of the city, the magnificent Tuscan countryside unfolds before you. Rolling hills dotted with vineyards, ancient olive groves, and picturesque villages create a stunning backdrop, perfect for leisurely conversation or serene reflection. Your driver, well-versed in the region's history and culture, is eager to share fascinating stories or allow you to enjoy the beauty in peaceful silence.
Arriving at your hotel in Siena, you'll be gently assisted with your luggage, feeling refreshed and invigorated. The seamless journey, tailored just for you, sets the perfect tone for your stay in this enchanting medieval city.
In the afternoon, you'll embark on a private walking tour through the medieval hill town of Siena, nestled in the heart of Tuscany and renowned for the Palio, the exhilarating horse race that electrifies Piazza del Campo twice a year. With an expert local guide at your side, you'll explore the artistic and architectural marvels that make Siena, a UNESCO World Heritage Site since 1995, a treasure trove of history and culture.
Wander through the enchanting streets of this Tuscan gem, surrounded by the rolling vineyards and olive groves of Chianti. Your journey begins at Piazza del Campo, Siena's iconic central square, where the elegant Palazzo Pubblico, adorned with Lorenzetti's frescoes, and the towering Torre del Mangia stand in grandeur. Encircling the square, you'll find an array of aristocratic mansions, each with its own unique charm.
Discover the historical significance of the Fonte Gaia, a medieval marvel marking the terminus of the ancient waterworks, situated in the northwest corner of the piazza. The Church of San Domenico, also known as Basilica Cateriniana, awaits with its sacred relics of Santa Caterina, one of Siena's patron saints.
A short stroll brings you to Fonte Branda, once a vital water source for the city in the Middle Ages. As you meander along Siena's historic streets, you'll encounter the Gothic splendor of Palazzo Salimbeni, now home to the Monte dei Paschi di Siena bank, and the venerable Palazzo Tolomei, one of the city's oldest edifices.
No visit to Siena is complete without marveling at the magnificent Cathedral of Siena. This Tuscan Gothic masterpiece boasts an intricately inlaid marble mosaic floor and a breathtaking pulpit sculpted by Nicola Pisano from Carrara marble. Opposite the Cathedral's facade, the historic Hospital of Santa Maria della Scala, one of Europe's oldest hospitals, now serves as a fascinating museum.
With each step, your guide will unveil the layers of Siena's rich history, ensuring an unforgettable experience in this enchanting medieval city.
Day 2: Sacred and Savory: A Private Day Trip from Siena to Assisi and the Flavors of Umbria
Embark on a private day trip from Siena to Assisi, the birthplace of Saint Francis, and immerse yourself in the rich flavors of Umbria’s renowned extra virgin olive oil and the exquisite Umbrian wine, Sagrantino.
Begin your journey with a scenic drive to Assisi, where you will be warmly greeted by your knowledgeable guide. Your first stop is the magnificent Saint Francis Basilica, a three-tiered masterpiece. Explore the upper church, adorned with French Gothic architecture and frescoes by Cimabue. Descend to the lower church, home to Giotto’s renowned cross vault and the neo-Romanesque Crypt, which has housed St. Francis's tomb since 1818.
Continue to the Basilica of Santa Maria degli Angeli, where the Porziuncola, a modest stone chapel restored by St. Francis, awaits. This sacred site, where St. Francis discovered his calling, is revered as the holiest place for Franciscans.
Leaving Assisi behind, venture into the rolling Umbrian hills to visit a traditional oil mill. Here, you will learn about the production of authentic Umbrian organic extra virgin olive oil, celebrated for its distinctive taste and health benefits. Enjoy a guided tasting session, followed by a light lunch featuring local Umbrian delicacies.
The adventure doesn't end there. Proceed to Montefalco, the heart of Umbrian wine country, for a tour of a prestigious winery. Discover the intricate process of crafting Sagrantino di Montefalco, a wine symbolizing the essence of Umbria, made exclusively from native Sagrantino grapes and produced only in this region. Savor a selection of fine wines during a guided tasting session, appreciating the depth and character of this celebrated vintage.
This private tour is a unique opportunity to delve into the spiritual heritage of Saint Francis, relish the robust flavors of Umbrian olive oil, and indulge in the exceptional wines of Montefalco, creating memories to cherish forever.
Day 3: Timeless Tuscany: A Day Tour from Siena to San Gimignano, Chianti, and Monteriggioni
Embark on a captivating day tour from Siena to explore the enchanting Chianti wine region, renowned as one of Tuscany’s most beautiful landscapes. This journey will take you to the medieval gem of San Gimignano and the historic walled town of Monteriggioni, all at your own pace and with the luxury of a private driver at your disposal.
Begin your adventure in San Gimignano, famously known as “the town of the towers” Its medieval skyscrapers, visible from miles away, tell a story of a small Etruscan village that flourished during the Middle Ages, thanks to its location on the Via Francigena pilgrim route from France to Rome. Here, you can leisurely explore a treasure trove of art and history. Admire the Collegiata, a Romanesque Duomo adorned with stunning frescoes by Ghirlandaio and other masters, and visit the church of Sant'Agostino to see the exquisite frescoes by Benozzo Gozzoli. The archaeological museums, filled with Etruscan and Roman artifacts, offer a glimpse into the town’s ancient origins. Be sure to pause in Piazza della Cisterna for a taste of the town’s best gelato.
Next, delve into the heart of the Chianti region, dotted with charming medieval villages such as Greve in Chianti, Castellina in Chianti, Radda in Chianti, and Gaiole in Chianti. This picturesque area, stretching from Siena to Florence, is world-famous for its Chianti and Chianti Classico red wines. Each village invites you to wander its historic streets and perhaps visit a local winery, where you can savor the rich flavors of their esteemed Chianti wines amidst the rolling vineyards.
Conclude your tour with a visit to Monteriggioni, a strategically positioned walled city between Siena and Florence. Monteriggioni played a crucial role in the Middle Ages during the conflicts between these two powerful cities. Today, it stands as one of the most evocative medieval towns in Italy, with its intact defensive walls and timeless charm.
This full-day excursion offers a perfect blend of history, art, and the finest Tuscan wines, ensuring a day filled with unforgettable experiences and delightful discoveries.
As your magical day in the Chianti region comes to an end, your driver will bring you back to Florence, or you might choose to extend your Italian journey by traveling to Rome. This comprehensive tour guarantees a remarkable experience, filled with stunning landscapes, historical wonders, and exceptional wines.
F.A.Q.
- What is special about Siena?
Siena is a city of remarkable charm and historical significance, nestled in the heart of Tuscany, Italy. What makes Siena truly special is its well-preserved medieval character, which transports visitors back in time as they wander through its narrow, winding streets and ancient buildings. The city is a masterpiece of medieval architecture, with its buildings and layout largely unchanged since the 13th century.
One of Siena's most iconic features is the Piazza del Campo, often considered one of the most beautiful squares in the world. This shell-shaped piazza is the heart of Siena, where the city's vibrant life unfolds and where the famous Palio di Siena takes place. The Palio is a historic horse race held twice a year, in which different districts, or "contrade," of Siena compete with intense rivalry. The event is steeped in tradition, with pageantry and ceremonies that date back centuries, making it a living representation of the city's history and community spirit.
Siena is also renowned for its stunning Duomo, or Cathedral, a striking example of Italian Gothic architecture. The Duomo is adorned with intricate marble facades, elaborate sculptures, and breathtaking frescoes. Inside, visitors are treated to masterpieces by artists such as Donatello, Pisano, and Michelangelo. The cathedral's floors are a marvel in themselves, with intricate mosaics depicting biblical scenes and allegories.
Beyond its architecture and events, Siena is special for its artistic and cultural heritage. The city was a thriving center of art during the Middle Ages and the Renaissance, producing influential artists like Duccio di Buoninsegna and Simone Martini. The Museo dell'Opera del Duomo and the Pinacoteca Nazionale house many important works, offering a glimpse into Siena's rich artistic legacy.
Moreover, Siena's unique atmosphere is complemented by its strong sense of community. The city is divided into 17 contrade, each with its own identity, traditions, and even its own church and museum. These contrade are more than just neighborhoods; they represent a deep-rooted sense of belonging and pride for Sienese residents.
Lastly, Siena is celebrated for its local cuisine, which reflects the traditions of the Tuscan countryside. Dishes like pici (a type of thick pasta), ribollita (a hearty vegetable soup), and the famous panforte (a dense, spiced fruitcake) offer a taste of Siena's culinary heritage, enriched by the quality of local ingredients.
In essence, Siena is special because it is a living museum of medieval history, culture, and art, wrapped in a warm, welcoming atmosphere that makes every visitor feel like they have stepped into a different era.